Alliin

Alliin
IUPAC name	(2R)-2-amino-3-[(S)-prop-2- enylsulfinyl]propanoic acid
Other names	3-(2-Propenylsulfinyl)alanine (S)-3-(2-Propenylsulfinyl)-L-alanine 3-((S)-Allylsulfinyl)-L-alanine S-Allyl-L-cysteine sulfoxide
Identifiers
CAS number	556-27-4
SMILES	C=CCS(=O)CC(C(=O)O)N
Properties
Molecular formula	C6H11NO3S
Molar mass	177.22 g/mol
Appearance	White to off white crystalline powder
Melting point	163–165 °C (325–329 °F)
Solubility in water	Soluble
Hazards
MSDS	External MSDS
NFPA 704	1 1 0
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Alliin (al'-ee-in) is a sulfoxide that is a natural constituent of fresh garlic.^[1] It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin which is primarily responsible for the aroma of fresh garlic. Garlic has been used since antiquity as a therapeutic remedy for oxygen toxicity, and when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical scavenging properties, possibly owing to the alliin contained within.^[2]

When the effect of alliin is observed on blood cells in vitro, a noted increase in the engulfing capacity of phagocyting cells is seen.^[3]

References

1. ^ Iberl, B et al. (1990). "Quantitative Determination of Allicin and Alliin from Garlic by HPLC". Planta Med 56: 320–326. doi:10.1055/s-2006-960969. 
2. ^ Kourounakis, PN; Rekka, EA (November 1991). "Effect on active oxygen species of alliin and Allium sativum (garlic) powder". Res Commun Chem Pathol Pharmacol. 74 (2): 249–252. PMID 1667340. 
3. ^ Salman, H et al. (September 1999). "Effect of a garlic derivative (alliin) on peripheral blood cell immune responses". Int J Immunopharmacol. 21 (9): 589–597. doi:10.1016/S0192-0561(99)00038-7. PMID 10501628.